Effect of the sulfur-covering group on the antiradiation activity of substituted 2-aminoethanethiols

Westland, Roger D.; Mouk, Mary Lou; Holmes, J. L.; Cooley, R. A.; Hong, Jean S.; Grenan, Marie M.

doi:10.1021/jm00279a022

Cited by 10 publications

(1 citation statement)

References 3 publications

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“…17 Moreover various sulfur compounds have been found to have other biological properties. [22][23][24][25] In view of these reports and in continuation with our previous work in the synthesis of biologically active heterocycles, [26][27][28][29][30] in this article we detail our synthesis of some new heterocycles with 1-phenyl-5-(thiophen-2-yl)-pyrazole moiety.…”

Section: Introductionmentioning

confidence: 74%

Synthesis and Characterization of Some New Heterocycles Incorporating the 1-Phenyl-5-(2-thienyl)pyrazole Moiety

Abdel‐Wahab

El-Ahl

2010

Phosphorus, Sulfur, and Silicon and the Related Elements

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1-Phenyl-3-(2-thienyl)-1H-pyrazole-5-carbohydrazide 4 was prepared from 2-acetylthiophene by reaction with diethyl oxalate and phenylhydrazine followed by hydrazine hydrate. The reaction of the hydrazide 4 with phthalic anhydride, aromatic aldehydes, and alkene derivatives gave imide 5, hydrazones 6a-d, and bis-pyrazoles 7 and 8, respectively, while its reaction with phenyl isothiocyanate led to thiosemicarbazide 9. The reaction of the latter with ethyl bromoacetate and phenacylbromide afforded 4-thiazolidinone 10 and 1,3-thiazole 11 derivatives, respectively. Reaction of 4 with carbon disulfide in the presence of potassium hydroxide gave potassium hydrazinecarbodithioate derivative 12, which was used as a starting material in the preparation of 2-thioxothiazol-3(2H)-yl)-5-(2-thienyl)-1H-pyrazole-3-carboxamide 14; 1,3,4-thiadiazol-2(3H)-ylidene)-1-phenyl-5-(2-thienyl)-1H-pyrazole-3-carbohydrazides 16a-c; 4-amino-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)pyrazole derivative 13; Schiff bases 17a,b; and 1,2,4-triazolo[3,4-b][1,3,4]thiadiazine derivatives 18 and 19a-e.

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Section: Introductionmentioning

confidence: 74%

Synthesis and Characterization of Some New Heterocycles Incorporating the 1-Phenyl-5-(2-thienyl)pyrazole Moiety

Abdel‐Wahab

El-Ahl

2010

Phosphorus, Sulfur, and Silicon and the Related Elements

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Radiosensitizers and Radioprotective Agents

Bump¹,

Hoffman²,

Foye

2003

Burger's Medicinal Chemistry and Drug Discovery

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Various approaches have been developed for diminishing the effects of radiation on normal tissues or enhancing tumor cell killing by ionizing radiation. An important potential use for these agents is to modify the outcome of radiation therapy. Potential radioprotectors or radiosensitizers are organized in this review according to mechanism of action. Most of the agents studied are believed to act by reacting with DNA radicals that are produced within milliseconds of exposure to ionizing radiation. According to this mechanism, protectors restore a single electron to electron‐deficient radicals, preventing degradation of the structure of DNA, whereas sensitizers, such as molecular oxygen or nitroimidazoles, form adducts with these radicals, resulting in damage fixation. WR2721 (Ethyol) is the best‐characterized chemical radioprotector. Preferential activation of WR2721 in certain normal tissues by removal of a phosphate group provides a rationale for selective protection of these tissues. Cytokines and biological modifiers represent an important emerging class of radioprotectors that may be particularly useful in modifying bone marrow injury. Nitroimidazoles have been the most widely studied chemical radiosensitizers. Although clinical results with nitroimidazoles have not been impressive, the potential for this approach has not been fully explored, given that the doses that can be administered have been limited by drug toxicity and supplemental strategies, such as concurrent depletion of endogenous protectors, have not been explored in the clinic. Modifiers of tumor oxygenation represent an important class of radiosensitizers that are currently generating considerable clinical interest. RSR13, a modifier of the oxygen affinity of hemoglobin, is highlighted as an example of the process of drug development for this type of agent.

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ChemInform Abstract: DER EINFLUSS DER SCHWEFEL‐SCHUTZGRUPPEN AUF DIE STRAHLENSCHUTZWIRKUNG SUBSTITUIERTER 2‐AMINOAETHYLMERCAPTANE

Westland¹,

Mouk²,

Holmes³

et al. 1973

Chemischer Informationsdienst

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Effect of the sulfur-covering group on the antiradiation activity of substituted 2-aminoethanethiols

Cited by 10 publications

References 3 publications

Synthesis and Characterization of Some New Heterocycles Incorporating the 1-Phenyl-5-(2-thienyl)pyrazole Moiety

Synthesis and Characterization of Some New Heterocycles Incorporating the 1-Phenyl-5-(2-thienyl)pyrazole Moiety

Radiosensitizers and Radioprotective Agents

ChemInform Abstract: DER EINFLUSS DER SCHWEFEL‐SCHUTZGRUPPEN AUF DIE STRAHLENSCHUTZWIRKUNG SUBSTITUIERTER 2‐AMINOAETHYLMERCAPTANE

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